Managing Difficult Workplace Conversations

There comes a point in every person’s career where they have to have a difficult conversation with their boss. Whether it’s over an unfair performance review, being looked over for a well-deserved promotion, or a fundamental disagreement over the way you are being treated, the fact of it is there’s no way to go through your career without having a tough chat with your boss at some point.

While it’s a scary prospect for the best of us, there are ways to prepare and manage these conversations to keep them from being too intimidating to handle.

Arrive prepared and with permission

Storming into your boss’ office will never start the chat on the right foot — make sure you have permission and time allocated for your conversation and ensure you walk through the door prepared and in control of your emotions. Walking in crying won’t earn you any favour with your boss.

Don’t talk in circles

Know what you’re saying, why you’re saying it, and how to say it concisely. Make your point early and make it clearly, or else you risk both confusing your boss and giving them the chance to come off on top of your conversation.

Listen to their perspective and argument

If they’re good enough to listen to what you have to say, give them the chance to air their grievances and stance on the issue. Take the time to listen to their opinion and actually listen to what they have to say — it might not totally sway your opinion, but it will inform it, and put you on a more equal, fair footing.

Be prepared to negotiate

It’s unlikely you’ll get exactly what you want, but be prepared to hold your own and fight for your claim. By negotiating, you can prove you’re a fair player without losing out completely, and make the difficult conversation far easier to manage.

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The team at Working Women are a diverse force, encompassing a wide range of backgrounds and a wealth of experience. With contributors from all levels of the workforce, we provide the best advice from real women in the workplace.